TW461884B - Process to continuously prepare an aqueous mixture of ε-caprolactam and ε-caprolactam precursors - Google Patents

Process to continuously prepare an aqueous mixture of ε-caprolactam and ε-caprolactam precursors Download PDF

Info

Publication number: TW461884B
Authority: TW; Taiwan
Prior art keywords: catalyst; patent application; scope; caprolactam; metal
Prior art date: 1998-09-03

Application number

TW087115614A

Other languages

English (en)

Chinese (zh)

Inventor

Robert Pestman

Lieshout Lambertus Hubertu Van

Original Assignee

Dsm Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-09-03

Filing date

1998-09-18

Publication date

2001-11-01

1998-09-18 Application filed by Dsm Nv filed Critical Dsm Nv

2001-11-01 Application granted granted Critical

2001-11-01 Publication of TW461884B publication Critical patent/TW461884B/zh

Links

JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 67
239000000203 mixture Substances 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title claims description 38
239000002243 precursor Substances 0.000 title claims description 15
230000008569 process Effects 0.000 title description 2
239000003054 catalyst Substances 0.000 claims abstract description 69
229910052751 metal Inorganic materials 0.000 claims abstract description 40
239000002184 metal Substances 0.000 claims abstract description 40
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 36
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 29
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 25
229910021529 ammonia Inorganic materials 0.000 claims abstract description 18
238000006268 reductive amination reaction Methods 0.000 claims abstract description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 15
229960002684 aminocaproic acid Drugs 0.000 claims abstract description 14
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims abstract description 13
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims abstract description 12
-1 alkyl 5-formylvalerate Chemical compound 0.000 claims abstract description 12
150000002739 metals Chemical class 0.000 claims abstract description 12
229910002804 graphite Inorganic materials 0.000 claims abstract description 9
239000010439 graphite Substances 0.000 claims abstract description 9
229910052799 carbon Inorganic materials 0.000 claims abstract description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 10
239000002245 particle Substances 0.000 claims description 9
230000002829 reductive effect Effects 0.000 claims description 9
239000002002 slurry Substances 0.000 claims description 8
CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical group CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
230000002079 cooperative effect Effects 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
229940125782 compound 2 Drugs 0.000 claims 2
238000004945 emulsification Methods 0.000 claims 2
229910000449 hafnium oxide Inorganic materials 0.000 claims 2
WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 claims 2
OQLKNTOKMBVBKV-UHFFFAOYSA-N hexamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCCOC1=CC=C(C(N)=N)C=C1 OQLKNTOKMBVBKV-UHFFFAOYSA-N 0.000 claims 2
229960001915 hexamidine Drugs 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 2
210000002784 stomach Anatomy 0.000 claims 2
239000013589 supplement Substances 0.000 claims 2
150000001875 compounds Chemical class 0.000 abstract description 7
PNPPVRALIYXJBW-UHFFFAOYSA-N 6-oxohexanoic acid Chemical compound OC(=O)CCCCC=O PNPPVRALIYXJBW-UHFFFAOYSA-N 0.000 abstract description 2
239000002904 solvent Substances 0.000 abstract description 2
ZLHYDRXTDZFRDZ-UHFFFAOYSA-N epsilon-aminocaproamide Chemical compound NCCCCCC(N)=O ZLHYDRXTDZFRDZ-UHFFFAOYSA-N 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 abstract 1
229910001928 zirconium oxide Inorganic materials 0.000 abstract 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
239000007858 starting material Substances 0.000 description 8
230000008901 benefit Effects 0.000 description 6
230000000694 effects Effects 0.000 description 6
229910052759 nickel Inorganic materials 0.000 description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
229910000423 chromium oxide Inorganic materials 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
YCYMCMYLORLIJX-UHFFFAOYSA-N 2-propyloctanoic acid Chemical compound CCCCCCC(C(O)=O)CCC YCYMCMYLORLIJX-UHFFFAOYSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
NCFJODHIQVLMQF-UHFFFAOYSA-N Methyl 2-methylhexanoate Chemical compound CCCCC(C)C(=O)OC NCFJODHIQVLMQF-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
GKJRZSWZJPEPLF-UHFFFAOYSA-N methyl 2-propyloctanoate Chemical compound CCCCCCC(CCC)C(=O)OC GKJRZSWZJPEPLF-UHFFFAOYSA-N 0.000 description 2
BSBYQAYWPXHLPQ-UHFFFAOYSA-N methyl 6-oxoheptanoate Chemical compound COC(=O)CCCCC(C)=O BSBYQAYWPXHLPQ-UHFFFAOYSA-N 0.000 description 2
238000010951 particle size reduction Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
229910001925 ruthenium oxide Inorganic materials 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
CUZLVVPSRFJTRR-UHFFFAOYSA-N 2-butyl-2-methylheptanoic acid Chemical compound CCCCCC(C)(C(O)=O)CCCC CUZLVVPSRFJTRR-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000009295 crossflow filtration Methods 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
KJLFZWJDCDJCFB-UHFFFAOYSA-N nickel(ii) titanate Chemical compound [O-2].[O-2].[O-2].[Ti+4].[Ni+2] KJLFZWJDCDJCFB-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Measurement Of Unknown Time Intervals (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

TW087115614A 1998-09-03 1998-09-18 Process to continuously prepare an aqueous mixture of ε-caprolactam and ε-caprolactam precursors TW461884B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP98202943A EP0984002A1 (de)	1998-09-03	1998-09-03	Verfahren zur kontinuierlichen Herstellung von einem wässrigen Gemisch von Epsilon-Caprolactam und Epsilon-Caprolactamvorläufern

Publications (1)

Publication Number	Publication Date
TW461884B true TW461884B (en)	2001-11-01

Family

ID=8234084

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW087115614A TW461884B (en)	1998-09-03	1998-09-18	Process to continuously prepare an aqueous mixture of ε-caprolactam and ε-caprolactam precursors

Country Status (13)

Country	Link
US (1)	US6452002B2 (de)
EP (2)	EP0984002A1 (de)
JP (1)	JP2002524441A (de)
KR (1)	KR20010073078A (de)
CN (1)	CN1142907C (de)
AT (1)	ATE264300T1 (de)
AU (1)	AU5535699A (de)
CA (1)	CA2342364A1 (de)
DE (1)	DE69916465T2 (de)
ID (1)	ID29478A (de)
MY (1)	MY121373A (de)
TW (1)	TW461884B (de)
WO (1)	WO2000014062A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1251122A1 (de) *	2001-04-17	2002-10-23	Dsm N.V.	Verfahren zur Herstellung von Epsilon-Caprolactam
KR100667006B1 (ko) *	2006-09-22	2007-01-12	주식회사 도화종합기술공사	공동구내 지중배전 케이블 지지앵글 수평유지 장치
CN101747248B (zh) *	2008-12-03	2012-08-22	中国科学院大连化学物理研究所	一种由5-甲酰基戊酸甲酯制备己内酰胺的方法
JP5512202B2 (ja) *	2009-09-14	2014-06-04	株式会社クラレ	β，β−ジメチル−ε−カプロラクタムの製造方法
US8946411B2 (en)	2012-02-23	2015-02-03	Rennovia, Inc.	Production of caprolactam from adipic acid
CN112300047B (zh) *	2019-08-01	2023-02-07	凯特立斯（深圳）科技有限公司	一种串联还原胺化合成手性内酰胺的方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0150295A3 (de) *	1983-12-19	1988-03-30	Allied Corporation	Selektive Herstellung von N-substituierten Amiden unter Verwendung von Cu(O)/Metalloxid-Katalysator-Zusammensetzungen
JPS62169769A (ja) *	1986-01-23	1987-07-25	Mitsubishi Heavy Ind Ltd	ε−カプロラクタムの合成方法
DE3602378A1 (de) *	1986-01-28	1987-07-30	Basf Ag	Verfahren zur herstellung von 6-aminocapronsaeureestern
DE3602377A1 (de) *	1986-01-28	1987-07-30	Basf Ag	Verfahren zur herstellung von caprolactam
MY116498A (en) *	1995-03-01	2004-02-28	Dsm Ip Assets Bv	Process for the preparation of é - caprolactam
US5700934A (en)	1995-03-01	1997-12-23	Dsm N.V.	Process for the preparation of epsilon-caprolactam and epsilon-caprolactam precursors
US5717089A (en) *	1995-03-01	1998-02-10	Dsm N.V.	Process for the preparation of E-caprolactam
US5652362A (en) *	1996-05-06	1997-07-29	Industrial Technology Research Institute	Preparation of caprolactam
EP0826666A1 (de) *	1996-09-02	1998-03-04	Dsm N.V.	Verfahren zur Herstellung von epsilon-Caprolactam
US5877314A (en)	1997-02-14	1999-03-02	Dsm N.V.	Process to continuously prepare an aqueous mixture of episilon caprolactum and episilon caprolactum precursors
US5977356A (en) *	1997-07-02	1999-11-02	Industrial Technology Research Institute	Process for preparing caprolactam

1998
- 1998-09-03 EP EP98202943A patent/EP0984002A1/de not_active Withdrawn
- 1998-09-18 TW TW087115614A patent/TW461884B/zh not_active IP Right Cessation
1999
- 1999-08-12 MY MYPI99003455A patent/MY121373A/en unknown
- 1999-09-01 WO PCT/NL1999/000544 patent/WO2000014062A1/en not_active Ceased
- 1999-09-01 DE DE69916465T patent/DE69916465T2/de not_active Expired - Lifetime
- 1999-09-01 AU AU55356/99A patent/AU5535699A/en not_active Abandoned
- 1999-09-01 AT AT99941882T patent/ATE264300T1/de not_active IP Right Cessation
- 1999-09-01 KR KR1020017002639A patent/KR20010073078A/ko not_active Ceased
- 1999-09-01 CN CNB998104159A patent/CN1142907C/zh not_active Expired - Fee Related
- 1999-09-01 EP EP99941882A patent/EP1109781B1/de not_active Expired - Lifetime
- 1999-09-01 ID IDW20010519A patent/ID29478A/id unknown
- 1999-09-01 CA CA002342364A patent/CA2342364A1/en not_active Abandoned
- 1999-09-01 JP JP2000568821A patent/JP2002524441A/ja active Pending
2001
- 2001-03-01 US US09/795,706 patent/US6452002B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2342364A1 (en)	2000-03-16
DE69916465T2 (de)	2005-03-24
WO2000014062A8 (en)	2000-06-08
WO2000014062A1 (en)	2000-03-16
DE69916465D1 (de)	2004-05-19
JP2002524441A (ja)	2002-08-06
KR20010073078A (ko)	2001-07-31
EP0984002A1 (de)	2000-03-08
EP1109781A1 (de)	2001-06-27
US20020007058A1 (en)	2002-01-17
US6452002B2 (en)	2002-09-17
ID29478A (id)	2001-08-30
CN1315941A (zh)	2001-10-03
EP1109781B1 (de)	2004-04-14
ATE264300T1 (de)	2004-04-15
AU5535699A (en)	2000-03-27
MY121373A (en)	2006-01-28
CN1142907C (zh)	2004-03-24

Legal Events

Date	Code	Title	Description
2002-03-07	GD4A	Issue of patent certificate for granted invention patent
2006-08-11	MM4A	Annulment or lapse of patent due to non-payment of fees

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